Changes are coming to two Northwest Side wards, though just one of them is guaranteed a new alderman.

The 30th Ward will definitely get a new face in the City Council, but both candidates in the runoff are linked to well-known political figures. Jessica Gutiérrez is the daughter of former U.S. Rep. Luis Gutiérrez, and political newcomer Ruth Cruz has the backing of retiring Ald. Ariel Reboyras.

The 36th Ward, meanwhile, might see incumbent Ald. Gilbert Villegas return for a third term. But the ward itself bears little resemblance to its longtime boundaries after aldermen drastically reconfigured it in a fit of political pique during last year’s ugly citywide remap fight. Chicago Teachers Union-backed candidate Leonor “Lori” Torres Whitt is trying to take him out.

[ Chicago ward map proposal blasted as ‘backroom deal’ and a loss for city’s Latinos; agreement means voters won’t decide on new boundaries ]

The races in the two wards share more than just some boundary lines. Political allegiances are also playing a role.

After Luis Gutiérrez endorsed Villegas in his unsuccessful run in the Democratic primary against Delia Ramirez for the U.S. Congress last year, Ramirez and some of her left-leaning allies have thrown their support to Cruz in the 30th Ward aldermanic race versus Gutiérrez’s daughter.

In the 36th Ward race, Villegas is hammering Torres Whitt because she had full homeowner property tax exemptions for two properties on the same block in Humboldt Park last year. Property owners are allowed only one such exemption, which lowers the tax bill for the home to which it is applied.

During an interview with the Tribune, Torres Whitt said she was entitled to the exemptions. But after the Tribune made inquiries, the Cook County assessor’s office last week sent Torres Whitt and her husband a notice informing the couple they apparently owed $736.67 for an exemption they should not have received for one building.

While that amount is minuscule given the size of local property tax levies that go to Chicago Public Schools and other government organizations, Villegas said it’s a matter of principle.

“It’s hypocritical for her to talk about education and schools while she illegally claimed multiple homeowner exemptions, reducing the amount of money schools receive,” he said. “It’s dishonest.”

[ Want to know what ward you live in? Explore the Tribune’s interactive map. ]

Torres Whitt’s husband, Booker Whitt, said in a statement that the two exemptions were a mistake. He didn’t realize he was entitled to only one at a time, he said, and the assessor’s office advised him to apply the exemption to one property without informing him he would need to remove it from the other.

He said they paid as soon as they received the notice. An assessor’s office spokesman confirmed the payment came in.

Torres Whitt sits on the CTU Executive Board and teaches Spanish at Monroe Elementary School. She said she is better positioned than Villegas to represent the new ward, which resembles a teeter-totter slanting from the Far Northwest Side’s Dunning neighborhood all the way southeast to the West Town area.

[ Shaped like a playground seesaw, new 36th Ward brings three challengers looking to knock off incumbent ]

“I get to bring to City Council a set of lenses that no one else has,” she said. “It is important for me and for the people I represent to be able to understand the Chicago that everyone lives in. When I think about what this ward looks like, everyone’s lived experience is different.”

Growing up in Humboldt Park and attending public schools, Torres Whitt said, she and her siblings and friends had lots of after-school programs and activities at parks to give them something to do. Making Chicago neighborhoods safer by pushing for more of those kinds of investments to keep kids off the streets would be a focus if she gets elected, she said.

Villegas noted he’s already championed programs such as the city’s guaranteed income initiative that help address the root causes of violence. And he said he’ll continue his commitment to “funding police at the proper levels.”

[ ‘Insane.’ ‘Obviously wrong.’ ‘Not a good thing.’ The new 36th Ward would stretch from the Far Northwest Side to West Town, baffling its future residents. ]

City Council colleagues redrew the 36th Ward as part of the decennial U.S. census remap process while Villegas fought unsuccessfully as chair of the council Latino Caucus for more majority-Latino wards. He’s now running for reelection in a convoluted district that includes lots of voters who don’t know him as well as those he’s represented for the past two terms.

While Torres Whitt is backed by the CTU and its allies, Villegas got an endorsement from the Illinois Network of Charter Schools and the Get Stuff Done political action committee, which is chaired by a former adviser to Mayor Rahm Emanuel.

The Get Stuff Done PAC, which is an independent expenditure committee that can’t coordinate with candidates, reported spending $48,257 on behalf of Villegas’ candidacy so far, and $7,500 to oppose Torres Whitt, according to the Illinois State Board of Elections. The Chicago Teachers Union PAC has spent $70,285 on mailers supporting Torres Whitt, according to the campaign finance records.

Villegas got 46.5% of the vote in the four-candidate first round race, while Torres Whitt got 30%.

The 30th Ward, meanwhile, twists from Belmont Central north through part of Portage Park and east into Old Irving Park. It’s an open seat, but the race is in many ways a familiar one.

The bad blood between Jessica Gutiérrez and Reboyras is getting a second straight airing. Reboyras beat her 52% to 48% in the 2019 runoff, then announced he was retiring at the end of this term after two decades on the council.

He’s putting his support and money behind Cruz, a Roosevelt University administrator who’s in her first political campaign. Reboyras has contributed $10,000 to Cruz, according to campaign finance records.

Both candidates are jabbing at each other for their connections. Cruz said Gutiérrez is riding on her father’s coattails.

“We’re done with old dynasties. We’re done with political families,” Cruz said of Gutiérrez. “We’re now in an era, in a time when the community comes first.”

Gutiérrez countered that Reboyras wants Cruz to continue his failed policies.

“He’s retiring? He’s not really retiring. He’s putting in a puppet in the 30th Ward, and we’ve seen it time and time again in Chicago,” Gutiérrez said. “She is his hand-chosen, his hand-picked choice.”

Gutiérrez got nearly 38% in the four-candidate first round election this year, while Cruz got 27%.

Reboyras has never been considered one of the City Council’s more progressive members, but with Ramirez’s endorsement Cruz also has picked up some progressive backing in her campaign.

“I’m building a coalition, uniting people across the board,” Cruz said.

The Illinois Network of Charter Schools, meanwhile, endorsed Gutiérrez, which she said reflects her work to build unity in the ward.

“We’re going to have to work with some of these organizations,” Gutiérrez said. “Listen, the truth is that Black and brown children are the majority of the students in attendance at charter schools. Charter schools are not going anywhere, and I think they’re going to need leadership in their community to sit at that table too. And that’s what I’m going to provide for them.”

jebyrne@chicagotribune.com

Twitter @_johnbyrne